The compounds of this invention are highly active, novel 3-substituted methyl sulfonylureas which are useful as herbicides and plant growth regulants.
EP-A-44,209 (Cognate) discloses herbicidal sulfonamides of formula ##STR1## wherein R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.1 is H, Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; and PA1 L is, among other values, CO.sub.2 R.sub.10, CONR.sub.3 R.sub.4, CN, Cl, Br, NR.sub.3 R.sub.4, S(O).sub.n R.sub.7, SO.sub.2 NR.sub.3 R.sub.4, OR.sub.9 and OC(O)R.sub.11. PA1 R.sub.9 and R.sub.10 are, among other values, H or CH.sub.3 ; PA1 R.sub.11 is COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group substituted with, among other values, CN, NO.sub.2, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, NR.sub.12 R.sub.13, SO.sub.2 NR.sub.15 R.sub.16, SC(O)R.sub.18, OC(O)R.sub.18 and OSO.sub.2 R.sub.17 ; PA1 R.sup.1 includes H, halogen, NO.sub.2, CN, C.sub.1 -C.sub.4 haloalkyl and COR.sup.18 ; and PA1 R.sup.2 includes H, halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; and PA1 R.sub.2 is C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyloxy, C.sub.3 -C.sub.6 alkenylthio, C.sub.3 -C.sub.6 alkynylthio, OCH.sub.2 CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 F, CHF.sub.2, OCF.sub.2 H, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 Cl, C.sub.2 -C.sub.6 alkyl substituted with 1-3 atoms of F or Cl or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio; PA1 X is CH or N; PA1 R.sub.6 and R.sub.7 include H or C.sub.1 -C.sub.4 alkyl; and PA1 R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or benzyl. PA1 m is 0 or 1; PA1 n is 0, 1 or 2; PA1 E is a single bond, CH.sub.2 or O; PA1 Q is a tetrazole or tetrazolinone; PA1 A includes pyrimidines and triazines; and PA1 R.sub.1 includes H, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 haloalkyl and C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 haloalkylthio or CN. PA1 R.sub.2 includes a variety of substituted methyl moieties; and PA1 A is one of seven heteroaromatic radicals. PA1 A includes substituted C.sub.1 -C.sub.6 alkyl and optionally substituted C.sub.2 -C.sub.6 alkenyl; and PA1 R.sub.2 includes H, halogen, C.sub.1 -C.sub.5 alkyl and C.sub.1 -C.sub.4 haloalkyl. PA1 R.sup.a is H, Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sup.b is H or CH.sub.3 ; and PA1 R.sup.c is Cl or Br. PA1 W is O or S; PA1 R is H or CH.sub.3 ; PA1 R.sub.X is H, F, Cl, CH.sub.3, OCH.sub.3, N(CH.sub.3).sub.2 or OCHF.sub.2 ; PA1 R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, CO.sub.2 R.sub.3, CONR.sub.4 R.sub.5, SO.sub.2 NR.sub.4 'R.sub.5 ', S(O).sub.n R.sub.6, OSO.sub.2 R.sub.7, C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, CH.sub.2 CN, C.sub.6 H.sub.5, ##STR12## R.sub.2 is ##STR13## R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, ##STR14## CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, or C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3, SCH.sub.3 or CN; PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.2 alkoxy; PA1 R.sub.4 ' is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.2 alkoxy; PA1 R.sub.5 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.5 ' is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.4 and R.sub.5 may be taken together to form --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --; PA1 R.sub.4 ' and R.sub.5 ' may be taken together to form --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --; PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl, --CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ; PA1 R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 or C.sub.3 -C.sub.6 cycloalkyl; PA1 R.sub.9 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.10 and R.sub.11 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.12 and R.sub.13 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.14 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.15 is H or CH.sub.3 ; PA1 R.sub.16 is H, C.sub.1 -C.sub.2 alkyl or F; PA1 R.sub.17 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.17 ' is H, C.sub.1 -C.sub.2 alkyl, CN, Cl, OCH.sub.3, SCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.18 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.19 is H, Si(CH.sub.3).sub.3 or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.20 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.21 is H, C.sub.1 -C.sub.3 alkyl or allyl; PA1 R.sub.22 is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 haloalkyl; PA1 R.sub.23 is H, CH.sub.3, Cl or Br; PA1 R.sub.24 is H or CH.sub.3 ; PA1 p is 1 or 2; PA1 n is 0, 1 or 2; PA1 A is ##STR15## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR16## m is 2 or 3; Q.sub.1 and Q.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 W is O. PA1 E is a single bond; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR19## Z is CH or N; R.sub.a is H or CH.sub.3 ; PA1 R.sub.23 is H; and PA1 R.sub.24 is H. PA1 R.sub.2 is --CH.sub.2 CN, --CH.sub.2 N.sub.3, ##STR20## and R.sub.17 ' is H, C.sub.1 -C.sub.2 alkyl, Cl or CN. PA1 R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with 1-3 F or Cl or 1 Br, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkenyl substituted with 1-3 F or Cl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, CO.sub.2 CH.sub.2 CH.sub.2 Cl, CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, CONH(C.sub.1 -C.sub.2 alkyl), CONCH.sub.3 (C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 NH(C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(C.sub.1 -C.sub.2 alkyl).sub.2, S(O).sub.n C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3, C.sub.6 H.sub.5 and R.sub.1 --A, R.sub.1 --B, R.sub.1 -- C, R.sub.1 --D, R.sub.1 --E, R.sub.1 --F, R.sub.1 --G, R.sub.1 --H, R.sub.1 --I, R.sub.1 --J, R.sub.1 --K, R.sub.1 --L, R.sub.1 --M, R.sub.1 --N, R.sub.1 --O, R.sub.1 --P, R.sub.1 --Q, R.sub.1 --R, R.sub.1 --S, R.sub.1 --T, R.sub.1 --U, R.sub.1 --V, R.sub.1 --W, R.sub.1 --X, R.sub.1 --Y, R.sub.1 --Z, R.sub.1 --AA, R.sub.1 --AB, R.sub.1 --AC or R.sub.1 --AD; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA1 R is H; PA1 R.sub.1 is F, Cl, Br, NO.sub.2, CH.sub.3, CF.sub.3 C.sub.1 -C.sub.2 alkoxy, allyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 NHCH.sub.3, CO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NHCH.sub.3 SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, SO.sub.2 C.sub.2 H.sub.5, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.2 H.sub.5, R.sub.1 --A, R.sub.1 --B, R.sub.1 --C, R.sub.1 --X, R.sub.1 --Z or R.sub.1 --AB; and PA1 R.sub.X is H.
EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula ##STR2##
South African Patent Application 84/2722 discloses herbicidal sulfonamides of formula ##STR3## wherein A is CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides of formula ##STR4## wherein R is H or CH.sub.3 ;
South African Patent Application 84/5216 discloses herbicidal sulfonylureas of the formula ##STR5## wherein R.sub.1 and R.sub.2 independently include H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio which are optionally substituted by halogen, NO.sub.2, OSO.sub.2 (C.sub.1 -C.sub.4 alkyl), OSO.sub.2 CF.sub.3 or C.sub.1 -C.sub.4 alkoxycarbonyl;
EP-A-204,513, published Dec. 10, 1986 discloses herbicidal sulfonylureas of the formula ##STR6## wherein G is O, S, SO or SO.sub.2 ;
EP-A-205,348, published Dec. 17, 1986, discloses herbicidal sulfonylureas of the formula ##STR7## wherein R.sub.1 includes halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, CO.sub.2 R.sub.3, CONR.sub.4 R.sub.5, SO.sub.2 NR.sub.4 R.sub.5 and certain heterocyclic aromatic moieties;
U.S. Pat. No. 4,515,626 discloses herbicidal 4-cyclopropyl pyrimidinyl and triazinyl benzenesulfonylureas.
U.S. Pat. No. 4,545,811 discloses herbicidal 4-(haloalkoxy or haloalkylthio)pyrimidinyl and triazinyl benzenesulfonylureas.
U.S. Pat. No. 4,510,325 discloses herbicidal compounds of the formula ##STR8## wherein X is O,S,SO or SO.sub.2 ;
EP-A-192,489 discloses herbicidal compounds of the formula ##STR9## wherein J is NHR.sub.2, NR.sub.3 R.sub.4 or NR.sub.2 'NR.sub.3 'R.sub.4 '.
U.S. Pat. No. 4,594,097 discloses herbicidal alkynylsubstituted benzenesulfonylureas.
U.S. Pat. No. 4,443,243 discloses herbicidal alkoxyalkynyl and thioalkynyl benzenesulfonylureas.
South African Patent Application 82/7439 discloses 4-aminopyrimidinyl and triazinyl benzenesulfonylureas.
South African Patent Application 83/6449 discloses herbicidal substituted-alkenyl benzenesulfonylureas.
EP-A-111,442 discloses herbicidal orthoheterocyclic benzenesulfonylureas.
South African Patent Application 84/2245 discloses herbicidal compounds of the formula ##STR10## wherein A is C.sub.1 -C.sub.6 haloalkyl; provided that A is not CF.sub.3 or CR.sup.a R.sup.b R.sup.c ;
U.S. Pat. No. 4,310,346 discloses herbicidal o-sulfonamide sulfonylureas.